DE231091C - - Google Patents

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Publication number
DE231091C
DE231091C DENDAT231091D DE231091DA DE231091C DE 231091 C DE231091 C DE 231091C DE NDAT231091 D DENDAT231091 D DE NDAT231091D DE 231091D A DE231091D A DE 231091DA DE 231091 C DE231091 C DE 231091C
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DE
Germany
Prior art keywords
diaminoanthraquinone
solution
sulfonic acid
acid
water
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DENDAT231091D
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German (de)
Publication of DE231091C publication Critical patent/DE231091C/de
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
    • C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
    • C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
    • C07C225/34—Amino anthraquinones

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

PATENTSCHRIFTPATENT LETTERING

- JV* 231091 -'■ KLASSE Mq. GRUPPE- JV * 231091 - '■ CLASS Mq. GROUP

Verfahren zur Darstellung von 1· 2-Diaminoanthrachinon.Process for the preparation of 1x2-diaminoanthraquinone.

Patentiert im Deutschen Reiche vom 28. September 1909 ab.Patented in the German Empire on September 28, 1909.

Es hat sich gezeigt, daß i-Halogen-2-aminoanthrachinon-3-sulfosäuren entstehen, wenn man die beim Sulfieren von 2 -.Aminoanthrachinon als erstes Produkt der Reaktion erhältliehe 3-Monosulfosäure mit ι Molekül Halogen behandelt. Die Konstitution der Körper ergibt sich daraus, daß bei der weiteren Einwirkung von Halogen die Sulfogruppe durch Halogen ersetzt 'wird unter Bildung von Dihalogen-2- · aminoanthrachinonen, und daß von diesen sich das Dibromderivat als identisch mit dem in der Patentschrift 158474, Kl. 22b, beschriebenen ι · 3-Dibrom-2-aminoanthrac'hinon erwiesen hat.It has been shown that i-halo-2-aminoanthraquinone-3-sulfonic acids arise if the sulphonation of 2-aminoanthraquinone 3-monosulfonic acid with 1 molecule of halogen is obtained as the first product of the reaction treated. The constitution of the body results from the fact that with further influence by halogen the sulfo group is replaced by halogen 'with formation of dihalogen-2- · Aminoanthraquinones, and that of these the dibromo derivative is identical to that in the Patent 158474, class 22b, described ι · 3-dibromo-2-aminoanthrac'hinon has proven.

Es wurde nun gefunden, daß die i-Halogen-2-aminoanthrachinon-3-sulfosäuren durch Behandeln mit Ammoniak in die 1 · 2-Diaminoanthrachinon-3-sulfosäure übergeführt werden, und daß diese beim Erhitzen mit verdünnten Säuren das in der Patentschrift 170562, Kl. 22 b, beschriebene und nach den Angaben der Patentschrift 167410, Kl. 12 0, nur schwer zugängliche 1 · 2-Diäminoanthrachinon liefert.It has now been found that the i-halo-2-aminoanthraquinone-3-sulfonic acids are converted into the 1 · 2-diaminoanthraquinone-3-sulfonic acid by treatment with ammonia, and that these are converted into the 1 · 2-diaminoanthraquinone-3-sulfonic acid when heated with dilute acids. Class 22 b, described and according to the information in the patent specification 167410, Class 12 0, provides 1 · 2-dieminoanthraquinone with difficulty.

Beispiel.Example.

ι Teil i-brom-2-aminoanthrachinon-3-sulfosaures Natrium wird mit 5 Teilen wäßrigem Ammoniak von 25 Prozent N i73-Gehalt, am zweckmäßigsten in Gegenwart von einem Katalysator, wie metallisches Kupfer, etwa 10 Stunden auf 100° erhitzt. Das abgeschiedene Reaktionsprodukt wird dann abfiltriert und gegebenenfalls durch Lösen in Wasser und Ausfällen mit verdünnter Salzsäure gereinigt.Part of i-bromo-2-aminoanthraquinone-3-sulfonic acid sodium is heated to 100 ° for about 10 hours with 5 parts of aqueous ammonia with 25 percent N i7 3 content, most conveniently in the presence of a catalyst such as metallic copper. The deposited reaction product is then filtered off and, if necessary, purified by dissolving it in water and precipitating it with dilute hydrochloric acid.

Claims (1)

Patent-An SPRU ch:Patent application: 3535 Die so erhaltene 1 · 2-Diaminoanthrachinon-3-sulfosäure bildet ein in. Wasser mit blauroter Farbe leicht lösliches Pulver, das Wolle in saurem Bade in bläulich roten Tönen färbt. Die Lösung in konzentrierter Schwefelsäure ist schwach gelb. Besonders charakteristisch für die 1 · 2-Diaminoanthrächinon-3-sulfosäure wie für das 1 · 2-Diaminoanthrachinon ist die blaue Farbe der Lösung in 8oprozentigem Oleum, die auffallenderweise beim Zusatz von konzentrierter Schwefelsäure beständig bleibt.The 1x2-diaminoanthraquinone-3-sulfonic acid thus obtained forms a powder that is easily soluble in water with a blue-red color, wool turns bluish red tones in an acid bath. The solution in concentrated sulfuric acid is pale yellow. Particularly characteristic of 1 · 2-diaminoanthraquinone-3-sulfonic acid as for the 1x2 diaminoanthraquinone, the blue color of the solution is 8% Oleum, which remarkably remains stable when concentrated sulfuric acid is added. Zur Überführung in das 1 · 2-Diaminoanthrachinon genügt es, die i-2-Diaminoanthrachinon-3-sulfosäure mit etwa der zehnfachen Menge 80 prozen tiger Schwefelsäure kurze Zeit zu erhitzen. Beim Eingießen der Lösung in Wasser scheidet sich das in Wasser unlösliche 1 · 2-Diaminoanthrachinon ab, das vollständig der in der Patentschrift 170562, Kl. 22 b, gegebenen Beschreibung entspricht.For conversion into the 1 · 2-diaminoanthraquinone it is sufficient to use the i-2-diaminoanthraquinone-3-sulfonic acid to be heated for a short time with about ten times the amount of 80 percent sulfuric acid. When pouring the Solution in water separates the water-insoluble 1 · 2-diaminoanthraquinone, the fully corresponds to the description given in patent specification 170562, class 22 b.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2424251A1 (en) * 1978-04-28 1979-11-23 Ciba Geigy Ag PROCESS FOR PREPARING 1,2-DIAMINOANTHRAQUINONE

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2424251A1 (en) * 1978-04-28 1979-11-23 Ciba Geigy Ag PROCESS FOR PREPARING 1,2-DIAMINOANTHRAQUINONE

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